


Business and Pleasure

by Cagedandfree



Series: Sam's Pleasure Buisness [1]
Category: Supernatural
Genre: Aftercare, Alternate Universe - College/University, Anal Fingering, Anal Play, Bisexual Dean Winchester, Bisexual Sam Winchester, Bottom Dean, Butt Plugs, Cock Cages, Dom/sub, Dom/sub Undertones, Enemas, F/M, Gags, Hand Jobs, I'll add more - Freeform, Kissing, Light Dom/sub, M/M, Medical Kink, Pullups, Sounding, Sub Dean, Top Sam, Toys, Vibrators, Wincest - Freeform, latex glove kink, medical fetish, rectal thermometers
Language: English
Status: Completed
Published: 2019-07-03
Updated: 2019-11-28
Packaged: 2020-06-03 04:39:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 4,368
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19456528
Author URL: https://archiveofourown.org/users/Cagedandfree/pseuds/Cagedandfree
Summary: Sam Winchester needs to pay for books for school so he offers his services. Things take an interesting turn when his client is his brother.changed it a bit took out Molly.





	1. Impala_67

Sam had always been into medical fetish and kinks since he was in high school, but now he’s in college and he can now really explore it. It started with scrubs and gloves, it was more that than anything else. Sam needed to make some money to pay for books and so he posted online that he was willing to meet up with anyone who had this interest. Being bisexual, Sam was open; he honestly wanted to meet likeminded people. To his surprise he got a hit. Someone that goes by the name “Impala_67”. 

Sam moved into his residence a week early for this. He chatted with Impala_67 and talked how it was more the latex glove fetish he had rather than the whole medical. Honestly, Sam liked that he found someone with the same fetish as him. He got a couple more hits and he made sure that they were alright.

Sam unpacked his clothes first. He was really happy that he and his roommate would have separate rooms so he doesn’t have to hide his medical stuff. He hung up his scrubs and in his closet he put his different types of gloves. Blue, white, purple and black. He placed different types of lubes, his enema kit, suppositories and rectal thermometer in a drawer. Sam had more medical things than actual things. 

He understood that he was being paid for this, but he didn’t mind. People had to do all sorts of things for money, there was no shame. Finally the day came. Sam told him to ask the front desk in res for Sam. He didn’t mind sharing his name with him. 

The two discussed that Sam would wear scrubs, his green ones. Sam bought some medical masks too, because he was curious about that and impala_67 liked it too. Sam had the white gloves ready, mask ready, scrubs on and lube on the table. 

There was a light knock on the door. Sam took a deep breath and opened the door. There stood his brother. Dean. He thought by the name it could be, but he wasn't too sure. Dean's face dropped when he saw his younger brother. 

"Sammy?" he whispered. 

“Dean.” Sam’s tone was soft and gentle. Dean looked up.

"Wha-what-what the hell man?!" Dean stepped inside. 

"I was about to ask the same thing." 

"Okay, well. I'm just going to go. I'll speak to you at Christmas." Dean reached for the door and Sam spoke. 

"Dean. Look, I need money for school and books."

"We're brothers" Dean said, his voice going quiet. 

"I know. Look, I'll give you your money back."

"How come you never said anything about this? Your kink?" Dean was trying to take things in.

"I thought you would judge me." Sam shrugged. 

"Look, since Michael...I've...." Dean trailed off. 

"No one has to know." Sam said. "I know we're brothers, but I-I am okay with this." 

"You are?" Dean blushed, looking down. 

“It’s okay to be nervous. I’m nervous too, I’ve never done this before.” Dean sighed a bit, eyebrows going up.

“You haven’t?” Sam noticed Dean relax. 

“No.”

“Me neither.” Dean blushed.

“See, it’s new to both of us.” Sam smiled. “Can I get you anything? Water?”

“No. No, thank you. I’m okay” Dean gave a half smile.

"Dean, if you want to leave, you can and we can never speak of this again."

"Would you judge me if i said I want to do this?" Dean couldn't look at Sam until there was a hand under his   
chin. Sam gave his older brother a warm smile.

“Should we go to my room then? We can just talk.” Sam wanted to make sure that Dean was as comfortable as possible.

“Sure.” Dean smiled. He started to relax more and more. 

Walking in his stomach flipped when he saw everything that Sam had set up. Dean shrugged off his jacket and Sam took it, placing it on the hook on the back of the door. Dean looked around the room more. He lived in res last year. 

“Dean. I want you to know that this is all about you. You want this to stop, you say stop. I am here to care for you. If you want to just talk about anything or gloves or whatever.” Sam smiled when he saw Dean blush and look away. 

“Could-could you maybe… kiss… me?” Dean asked.

Sam nodded and lightly cupped Dean’s check, stroking his thumb on his jawline. Dean leaned into his touch and Sam lightly kissed him. He kept it gentle and short, lingering before pulling away. Dean smiled, looking at Sam. Sam still kept his hand on Dean’s cheek.

“Thanks” Dean said quietly. 

“You’re a good kisser.” Sam admitted.

“Oh, thank you”

“Can I kiss you again?” 

Dean nodded and Sam kissed him, this time a little more passionately. Dean’s hand went to Sam’s chest. Sam stepped a bit closer, placing his other hand on Dean’s hip. Sam pulled away slightly, rubbing his nose against Dean’s. Giving him a quick kiss.

“I think I’m ready now” Dean’s voice was quiet.

“Yeah?” Sam asked sweetly and Dean nodded. “Okay. Get comfortable. You can take off your close or not.”

The boys broke contact and Sam stepped over to the table and grabbed the gloves. Dean took off his shoes, shirt and pants and boxers. Sam pulled on the right latex medical glove, giving it a snap. He pulled on the left on and Dean started to get hard. Sam kissed Dean, a gloved hand stroking up and down Dean’s rib cage. Sam reached down and gave a little squeeze.

Dean relaxed when Sam started to stroke him. His hand went to Dean’s face. Dean closed his eyes, lips parting. Sam lightly brushed his thumb against Dean’s lower lip. The little moan that came from Dean caused Sam to groan. Dean’s cock twitched in Sam’s hand. 

Sam’s thumb swiped against the tip.

“Ohhh” Dean moaned louder.

“Lay on the bed for me” Sam instructed. 

Dean laid down and Sam grabbed the medical mask and put it on. He pulled up a chair and sat down. Sam grabbed the lube and popped the cap. He poured some on his hand and started to stroke Dean some more.

“The doctor is going to take good care of you” Sam’s voice got a bit lower and Dean bucked his hips in response. Sam lightly rubbed against Dean’s hole, sliding a finger in. He found Dean’s prostate and rubbed at it.

Dean had only been with one guy before. He was also bi, like Sam. Dean had been with two girls, Jo and Anna. However he really hit it up with a guy he met in residence last year, Michael. They dated for a few months, but it didn’t work out. Since then, Dean had been scared to really go out and date.   
He had this fetish and Michael was the one that got weirded out by it. So when he saw Sam’s posting he decided to take a chance.

Dean gripped the sheets as Sam started to quicken his movements. Dean came, spilling on Sam’s gloves. Dean’s little pants made Sam happy.

“Good” Sam spoke, removing his finger from Dean’s ass and let go of Dean’s cock. 

“God, that was good” Dean said, catching his breath.

“I’m glad. Now, lay there while I clean you up” Sam’s voice still low.

Sam stripped off his gloves and pulled new ones on. He grabbed warm wash cloth and started to wipe Dean down. Sam put the cloth down, took the mask off and pulled the gloves off. Dean started to sit up. Sam saw that he looked a little down upset as he stood up.

“Hey, where are you going?” Sam asked gently, head titling a bit to the right. 

“Oh. I-uh- I thought we were done.” Dean looked down.

“Well yeah. But I told you I would take care of you, Dean. Aftercare. If you’re okay with that?”

“Oh. Yeah” Dean sat back down on the bed. 

Sam took his scrub top of and sat side Dean. He rubbed hand on his back, leaning over and kissing Dean’s temple. Dean reached out and a bit. Sam noticed and held his hand. Dean rested his head on Sam’s shoulder.

“Do-do you think maybe I could come back and we could both wear gloves. Maybe just talk. I know I would be paying, but hey, it’d be like therapy in a way.”

“Of course Dean. I would like that.”

“Yeah?” Dean looked up at Sam, hopeful.

“Yeah” Sam gave him a soft smile.


	2. Locked up

**Notes for the Chapter:**

> bit short

It’s been a month now since Dean started to pay a visit to his brother. Dean had told Sam that he masturbated with gloves almost once a day. Hearing that, Sam had plans for his older brother. Dean was scheduled to come Sam this weekend. Sam stopped charging Dean, and only had payments coming from Molly.

Sam got ready for is brother. He wore his green scrubs that Dean liked so much. He lined everything up on the desk. Dean knocked on the door and Sam opened it smiling at his brother. The eldest Winchester stepped in and Sam gave him a gentle kiss.

“Are you ready for this weekend Dean?” Sam asked and dean nodded. “Good. Now, I feel that you playing with yourself every day is a bit much, so as your doctor dom, I’ve decided that we are going to lock up your cock.” Sam’s gentle. 

“What?” Dean whispered. Sam cupped his cheeks and kissed him. 

“Just for tonight and part of tomorrow. Dean, do I know best?” 

“Yes doctor.”

“Good boy.” Dean kissed Sam. 

In Sam’s bedroom Dean stripped of his clothing and Sam pulled on white medical gloves and a medical mask. Dean eyed the table and his got a little nervous seeing a small plug.

“Sammy…” he started and Sam followed his gaze. 

“I thought we would also try a plug. If you do not want to, that’s very okay Dean. But that’s why I asked that you give yourself an enema.” Dean nodded.

“Okay, doctor. If you think it’s best.”

“I think it’s the best course of treatment right now. Please lay on the bed for me Dean. Feet on the bed.”

Dean did as his younger brother instructed and he heard the popping of the cap. He jumped when he felt gloves spread his ass cheek apart. Sam gave a little rub against Dean’s hole. Sam stepped away, lubing up the plug.

“This will feel a bit strange Dean. Please relax as much as you can.” 

Sam pushed the tip of the plug against Dean. When he felt him relax, he slid the plug in, holding it there. Dean let out a small whimper and Sam placed a caring hand on his thigh.

“There, it’s in. Just breathe Dean. You’re doing good” he encouraged.

“Feels funny” Dean whispered.

“I know, you you’ll get used to it.” 

When Sam was sure that Dean wouldn’t push it out he changed his glove and got the cock cage. He placed it on Dean, locking it and placing the key on the desk. Dean laid there, plugged and locked up. Sam sat by his brothers head and stroked his cheek with his gloved hand.

“It’s just for tonight, Dean.”

“I know.”

“Now, can you sit up? I’m going to sit behind you and hold you.”

“With gloves” Dean asked hopeful. 

“Of course”

“May I…wear gloves?” 

“I would like that” Sam smiled at his brother

Sam opened the cupboard and grabbed some gloves for Dean. He took his mask off and handed them to Dean, watching him pull them on. Sam sat with his back against the bed and Dean carefully sat between Sam’s legs. He wrapped an arm around Dean’s waist and Dean ran his gloved hands over Sam’s arm. Sam stroked his brother’s cheek.

“Is this alright, Dean?” Sam finally spoke.

“This is perfect.”

“Good.”

“Uh-Sammy. What’s with the diapers?” Dean noticed in Sam’s drawer.

“Oh. Those are for my other client. They’re into diapers as well as medical and gloves.”

“Oh. Interesting. Do they use them?” 

“Yes. And as a doctor, I clean them up.”

“That doesn’t bother you?”

“Not really. It’s what they like and they’re paying me.”

“Right.”

Sam watched as his brother relaxed and fell asleep in his arms. Sam kept stroking his face, neck, shoulders. A while later Dean woke up.

“Oh. Sorry for falling sleep.” He said.

“No need to be sorry Dean.” Sam kissed his shoulder. “Did you sleep well?”

“Yes I did” 

“Good. Open your mouth for me.” Dean did and Sam stuck two gloved fingers in “Be a good boy and suck for a while.” Dean sucked Sam's fingers. Sam smiled when Dean moaned


	3. release

**Notes for the Chapter:**

> short

Sam took the plug out when they went to bed, but Dean’s cock was still caged. He wondered what Sam had planned. In the morning, the cage was still on as they had breakfast. Finally Sam got in his green scrubs and had Dean sitting in the chair.

As Sam pulled on the white latex gloves and medical mask Dean’s eyes found a box Sam had that Dean never noticed before. There was a towel on the floor. Sam pulled a wheeling stool up and brought the box to the bed so he could reach.

“Your cage will come off and I’m going to let you cum.” Sam spoke.

“However, it will be from nipple stimulation.”

This was something Sam and Dean had talked about for a while. 

Sam opened the box and pulled out a nipple pump. He stood up and placed it on Dean’s right nipple pumping it up. He pulled out the left one and pumped up Dean’s nipple. He reached in and pulled out a ballgag. He opened his mouth and Sam placed it in, securing it.

“Please trust the doctor.” Sam said and Dean nodded. “Good boy.” Sam grabbed cuffs and cuffed Dean’s hands behind the chair. “This procedure will be a bit rough, so I’ll need to secure your hands.”

Sam took the cock cage off, Dean’s dick limp. A few minutes later Sam pulled the pumps off. He rolled Dean’s nipples with his gloved thumb and forefinger. Dean’s cock twitched he rubbed them and Dean’s cock got semi-hard.

“Good boy. Now this may hurt.” Sam reached into the box and pulled out a clamp placing it on his right nipple.

“MMPH” Dean let out a whine. 

Sam placed the left one on. The left on made Dean’s cock stand at attention and then drop a bit. Sam gave a tug on the clamps and twisted them. Sam watched as Dean’s cock bounced. Sam circled the clamps a few times before tugging them off.

“Look at me” Sam spoke, voice low.

Dean looked his brother in the eyes. Mask on his face, Sam rolled Dean’s nipples, tugged on them. Dean moaned and moaned, hips slightly bucking. A minute later Sam attached the clamps again, his gloved hand cupped his chin.

“Are you going to cum for me?” Sam got in Dean’s face and he grumbled. Sam tugged on the clamps.

“Hmmph” Dean cried out, jerking his hips. His dick hard now. 

Sam twisted the clamps, pulled them off again. Sam walked behind Dean took his gloved middle fingers and rubbed Dean’s nipples leaning in.

“Be a good boy for the doctor and cum” Sam whispered in his ear.  
Both men watches as Dean came on the chair and towel. Sam gave one final tug to Dean’s nipples. A gloved hand going to his throat.

“I’m so proud of you Dean. You took your treatment very well.” Sam whispered. 

Sam’s other hand went to stroking Dean’s cheek. A minute later when Dean’s breathing was even Sam took the mask off and kissed his brother’s temple.

“I’m going to untie you now Dean, clean you up.

Sam took the gag out, untied Dean’s arms, lifting him up as if he was light as a feather and laid him down on the bed. Sam grabbed a cloth and wiped Dean’s mouth from the drool and where it got on his chest. Sam got a warm cloth and wiped Dean’s cock. Sam praised him the whole time.


	4. tied up

**Notes for the Chapter:**

> Bit short

Dean stood naked in Sam’s room. His fingers were laced together and placed behind his head, elbows out. His legs were spread apart. Sam was wearing his green scrubs and snapped on white latex gloves. 

“Are you ready for your inspection?” Sam asked, adjusting his gloves.

“Yes” Dean breathed out.

Sam rubbed a hand on Dean’s chest, pinching his left nipple. Dean let out a moan. Sam then pinched his right nipple. Sam felt around his sides and Dean’s underarms. 

“Open your mouth” Sam instructed and Dean did.

Sam felt around Dean’s mouth with two fingers. pushing back. He inserted three fingers moving them in and out a bit. Sam reached down and rolled Dean’s balls in his hand and with his other hand squeezed his cock. Dean moaned quietly.

“Bed. Elbows and knees.”

Dean was quick to move. He gasped when a gloved finger probed at his hole. Sam spread his cheeks apart, dipping a finger in. He gave spank, causing Dean to buck his hips. Sam kept lightly probing Dean’s ass, rubbing his hole a few times.

“Good boy” Sam praised slipping the gloves off. “Now, time for the doctor to give you a slightly more humiliating treatment.”

“Yes doctor” Dean swallowed.

Sam kissed Dean, calming him. He gave a grin and got to work. Sam had Dean tied to the bed, ballgag in mouth. Sam snapped on white latex gloves, put on a medical mask, sat on the stool and wrapped his hand around the base of Dean’s shaft. Sam lubed up the butt plug and pushed it against Dean’s hole. It slid in with ease and Sam smiled behind the mask. 

Next Sam pulled a tray over that he bought and grabbed a wipe, holding the base of Dean’s cock. He wiped the tip and grabbed the lube and catheter. 

“This will be a bit uncomfortable, but I need you to breathe, Dean.” Sam instructed.

Dean whimpered behind the gag when he felt the lubed catheter enter in. Sam carefully got to work, making sure it was secure to the bag and attached the bag to a stand. Sam changed his gloves and grabbed the vibrator and turned it on. He placed it on Dean’s right nipple, causing him to cry out, when it was nice and hard, he placed it on the left nipple.

“Good boy.” Sam praised.

He grabbed the nipple clamps and clamped them to Dean’s nipples. Sam rubbed his gloved hands up and down Dean’s ribcage. Dean whimpered.

“What a beautiful sight. Poor little patient all tied up, plugged, catheter, nipple clamps.” Sam went and stroked Dean’s cheek. “Don’t worry, the doctor will take excellent care of you.” Dean whimpered “I’m going to leave you like this, for a bit.” Sam went back to stroking Dean’s ribcage.

Sam stepped back and between Dean’s legs and pulled down his green scrubs and took off his top and bottoms. Dean look at his naked brother, now only wearing gloves and a mask. Sam adjusted his gloves, staring at Dean, the whole time.

Sam wrapped his hand around his cock and started to stroke it. Seeing his brother so helpless made Sam so aroused. He couldn’t wait to play with his brother. After a few strokes Sam went and changed his gloves, sitting down at his desk, ready to do some homework.

“Hmm” Dean whimpered behind the gag.

“Don’t worry, the doctor is right here.” Sam reassured his sub.


	5. Chapter 5

**Notes for the Chapter:**

> Very short

Sam looked at his helpless brother. Sam stood up and walked over inspecting the catheter. He ran a gloved hand up his brother’s body.

“Poor desperate patient. You want the doctor to take care of you, don’t you?” Sam’s voice going a little darker. Sam tugged on the nipple clamps, causing Dean to cry out. “I’m here to care for you.”

Even with the mask, Dean could tell that the smile was sinister. Sam went and took the catheter out of Dean, placing it down. Sam wiped him and cleaned up a bit. Sam changed his gloves, pulling the white ones back on with a snap.

“Poor nipples must be so sensitive.” Sam gave a tug and Dean cried out again. “And your ass getting all nice and stretched for me.” 

Sam took the clamps off his brother’s nipples and took them in between his thumb and forefingers and twisted them. The latex gloves, made Dean’s cock twitch. Sam loved that his nipples were sensitive. Sam reached up and gripped Dean’s chin, the ball gag causing him to drool.

“Good little patient, all covered in drool. This is going to be fun.” Sam untied Dean’s legs and arms, grabbing a spreader bar. “Knees, arms through your legs” Sam explained

Dean did as he was told and rubbed a glove hand up Dean’s back and strapped him to the spreader bar. Sam walked over to the table and grabbed the lube, walking back. He have a spank to Dean’s ass, Dean gave a yelp.

“You like when I spank you?” Sam asked, massaging Dean’s ass. “That will be for next time, if you want.” Sam saw Dean nodded. 

Sam tugged at the plug, twisting it and moving it in and out. Sam pulled it out of Dean’s ass and squirted lube on his fingers, rubbing them together and then against Dean’s hole. He easily slid two fingers in, working them in and out, scissoring his fingers. 

“Good boy” Sam said.

Sam worked a third finger in Dean’s ass. Sam pulled his fingers out, poured lube on his hand and started Sam changed his gloves and grabbed a vibrating anal plug. He lubed it and slid it in and turned it on. Sam changed his glove once more and walked over to Dean’s head and undid the ball gag.

Sam stroked Dean’s cheeks with the latex gloves and he felt Dean relax against his hand, eyes closing a bit. He grabbed his cock and lightly opened Dean’s mouth. Dena looked up, drooling a bit and stuck his tongue out. Sam smiled at his reaction. 

Dean was grunting and moaning. Sam placed his cock in Dean’s mouth and Dean happily started to suck. The latex gloves calmed him as Dean started to tear up when Sam turned the vibrator up more, massaging his prostate.

“Such a good boy for the doctor.” Sam praised.

Sam pulled out of Dean’s mouth and watched as Dean started to cry out in pleasure as the pressure was building. Sam moved to the side and reached down, giving a few strokes to Dean’s cock, leaking pre-cum.

“Aaaah” Dean yelled as he came, panting from crying a bit from all the torture and pleasure his brother gave him.

“So good, Dean. You were so good for me.” Sam turned the vibrator off and pulled it out. 

He then undid the spreader bar, lifting his brother up and laying him down. He removed the toys from bed and grabbed a warm cloth and started to wipe him down. He took the mask off and kissed Dean’s forehead and wrapped him in a blanket. Sam got back in his scrubs and sat behind Dean and held him.

**Notes for the Chapter:**

> running out of ideas


	6. Chapter 6

Dean was in trouble. Sam had started giving him homework. A journal to fill out and he was to give check ins on moods and how he feels. Dean had missed a few days and Sam was worried about. When he finally got his brother and sub on the phone, Dean knew he was in trouble. He caught Sam up no the days, he was glad to hear Dean was busy. 

Dean stood naked, fingers linked behind his head, legs spread apart. Sam had his green scrubs on, and white latex gloves. Sam stood close to Dean, gripping his chin with his latex covered fingers.

“Do you know why you’re in trouble?”

“Yes, doctor” Dean responded.

“So you understand why you have to be punished.”

“Yes, doctor. I failed to-“Dean started, but Sam cut him off.

“No, Dean. You did not fail. You are an amazing sub. Please start again.”

“I forgot to” he dragged out and Sam nodded, smiling, encouraging him “To check in with you and to write in my journal.” 

“Good boy.” Sam praised. “I am so proud of you.” Dean blushed “I will be giving you a spanking, followed by your plug and cock cage.”

Dean nodded and Sam kissed him, his latex covered hand cupping Dean’s cheek. Sam wrapped Dean in a hug, holding him tight. Sam had Dean get on his elbows and knees, legs spread. Sam’s left hand rested on the small of Dean’s back.

*SMACK* 

“Ah!” Dean yelped.

“Very good. Nineteen more.” Sam said.

*SMACK* *SMACK* *SMACK*

Each smack came harder and harder. Alternating between each butt cheek. Dean’s gaps and moans made Sam smiled. When Sam was done, he rubbed Dean’s ass and sat down, pulling Dean onto his lap. He peppered his head with kisses and praises.

“Such a good boy, Dean.”

“Thank you, doctor.” Dean whispered.

A few minutes later Sam laid Dean down on the bed and told him to lifted his legs and spread them. Sam grabbed the cage and placed it on Dean, looking at his brother being so helpless. Dean closed his eyes when he heard the popping on the lube cap. 

Sam squirted some on his fingers and rubbed it against Dean’s hole, hearing him whimper. Dean clenched and relaxed when Sam pushed a finger against him. Sliding a finger in, Sam worked it in and out of Dean. He hit his prostate and Dean’s eyes shot open.

“There we go. Nice and easy, Dean. I’ll be giving you milking in the morning.”

Sam slipped a second finger in and scissor Dean open. Sam pulled his fingers out, lubed a bigger plug and pushed it against Dean who easily took it.

“There, all plugged up.”

Sam cleaned Dean up and slipped his gloves off and rolled Dean over.

**Author's Note:**

> Comment and kudos


End file.
